How a Portfolio Manager Applies Wall Street Principles to STR Investing | S02E32

What happens when a seasoned Wall Street portfolio manager enters the short-term rental game? In this episode, we sit down with Andy Newman, CEO of Newman Hospitality, to unpack the surprising parallels between financial portfolio management and building a successful STR (short-term rental) business.

With over a decade of experience in both banking and vacation rentals, Andy shares what most STR operators overlook — and how applying investment discipline, risk management, and diversification principles can be the difference between scaling sustainably and burning out.

Whether you’re an investor, operator, or just STR-curious, this episode delivers practical insights and honest reflections you won’t hear anywhere else.

What You'll Learn:

• The “1,500-Mile Rule” for reducing market and seasonality risk in your STR portfolio

• Why most people buy vacation rentals in the wrong places — and how to fix it

• The marketing mistake that slowed Andy’s growth for 5 years

• How to diversify STR investments like a true portfolio manager

• Why Vacasa’s national scaling strategy failed — and what’s working instead

• How to evolve from operator to CEO (and build a team that stays)

• The overlooked operational bottleneck costing STR companies thousands

• Andy’s thoughts on STR tech, guest experience, and what’s still missing in the space